Patent GB-494768-A (GB)
Title: Aromatic polyether chlorides
Filed: 1937-05-04
Abstract: b -Chloroalkoxyalkyl ethers of monoyhdric phenols substituted in the nucleus with an aliphatic hydrocarbon radicle of 8-18 carbon atoms are prepared by reacting the phenols with a b , b 1-dichlorodialkyl ether in the resence of a concentrated aqueous solution of an alkali-metal hydroxide.  Specified phenols are straight or branchedchain octyl-, decyl-, dodecyl-, hexadecyl-, oleyl- or octadecylphenols; the correspondingly substituted cresols or xylenols may also be used, and other nuclear substituents, e.g. a chlorine atom or a nitro or alkoxy group, may also be present.  The ethers used are of the type XCH2 CHROCHRCH2X, where X is chlorine and R is hydrogen or a methyl, ethyl, propyl, butyl, amyl or other alkyl group.  In the examples, (1) p-(a , a , g , g -tetramethylbutyl) phenol is condensed with b , b 1-dichlorodiisopropyl ether or (example 2) with b , b 1-dichlorodiethyl ether; (3) o-methyl-p-a , a , g , g -tetramethylbutyl) phenol or (example 4) o-chloro-p-(a , a , g , g -tetramethylbutyl) phenol, or (example 5) caprylphenol or (example 6) laurylphenol or (example 7) cetylphenol or (example 8) stearylphenol is condensed with b , b 1-dichlorodiethyl ether; (9) a higher alcohol fraction, obtained from the reaction of hydrogen with carbon monoxide, is condensed with phenol in the presence of zinc chloride, and the product is treated with b , b 1-dichlorodiethyl ether; (10) undecylphenol is treated with b , b 1-dichlorodiethyl ether.  The products may be converted into emulsifying agents by sulphonation of the benzene ring or by replacement of the terminal chlorine atom by a hydrophilic group.  Specifications 494,766 and 494,769 are referred to.ALSO:b -Chloroalkoxyalkyl ethers of monohydric phenols substituted in the nucleus with an aliphatic hydrocarbon radicle of 8-18 carbon atoms are prepared by reacting the phenols with a b , b 1-dichlorodialkyl ether in the presence of a concentrated aqueous solution of an alkali-metal hydroxide. Preferably, one mol. of the phenol is heated with 3-4 mols. of the dichlorodialkyl ether in the presence of 1-1,5 mol. of alkali hydroxide.  Specified phenols are straight or branched-chain octyldecyl-, dodecyl-, hexadecyl-, oleyl- or octadecyl-phenols; the correspondingly substituted cresols or xylenols may also be used, and other nuclear substituents, e.g. a chlorine atom or a nitro or alkoxy group, may also be present.  The ethers used are of the type XCH2CHROCHRCH2X, where X is chlorine and R is hydrogen or a methyl, ethyl, propyl, butyl, amyl or other alkyl group.  In the examples: (1) p-(a , a , g , g -tetramethylbutyl) phenol is condensed with b , b 1-dichlorodiisopropyl ether or (example 2) with b , b 1-dichlorodiethyl ether; (3) o-methyl-p-(a , a , g , g -tetramethylbutyl)phenol (made from o-cresol and diisobutylene in the presence of sulphuric acid) is condensed with b , b 1-dichlorodiethyl ether; (4) o-chloro-p-(a , a , g , g -tetramethylbutyl)-phenol is condensed with b , b 1-dichlorodiethyl ether; (5) sec.-octyl borate is condensed with phenol in the presence of boron fluoride, and the caprylphenol so obtained is treated with b , b 1-dichlorodiethyl ether; (6) lauryl alcohol is heated with phenol in the presence of zinc chloride, and the laurylphenol so obtained is condensed with b , b 1-dichlorodiethyl ether; (7) cetylphenol (prepared from phenol and cetyl alcohol in the presence of zinc chloride) is condensed with b , b 1-dichlorodiethyl ether; (8) stearylphenol (prepared from phenol and n-octadecanol-1 in the presence of zinc chloride) is condensed with b , b 1-dichlorodiethyl ether; (9) a higher alcohol fraction, obtained from the reaction of hydrogen with carbon monoxide, is condensed with phenol in the presence of zinc chloride, and the product is treated with b , b 1-dichlorodiethyl ether; (10) phenol and 5-ethylnonanol-2 are condensed in the presence of zinc chloride and the undecylphenol so obtained is treated with b -b 1-dichlorodiethyl ether.  The products may be converted into detergents and emulsifying agents by sulphonation of the benzene ring or by replacement of the terminal chlorine atom by a hydrophilic group.  Specifications 494,766 and 494,769 are referred to.